During the late summer and early fall of 2025 I fell from an airplane more than 30 times… on purpose. The result? I became a licensed skydiver. What? Why now?
For those of you who haven’t followed our journey at Little Engine Ventures, we acquired Skydive Indianapolis in April 2019 without me having been skydiving. I think we were the first non-skydiver owners in the industry. At the time I was not opposed to those who chose to skydive but it simply wasn’t on my to-do list. The whole thing seemed to me like a mispriced investment. I was just being logical. On a personal note, I was over the weight limit. I couldn’t go. As time passed the weight joke became a convenient excuse. The reality was that I was afraid of heights. What if it went wrong for me? All the usual reasons to not go! But, beyond that, I still really just didn’t want to go.
In early November 2024 I began a weight loss journey. In the first few weeks of that journey I began to day dream about skydiving. I wanted to do it. If I lost weight I wouldn’t have that excuse. So, why not get my mind around going? Skydiving had officially come onto my todo list. Fast forward 10 months and I had lost over 60 pounds and was feeling much healthier. Time to celebrate. Time to skydive. And then I loved it. I just kept going and earned my A-license.
Skydiving is a bucket list experience for many people. It is a once in a lifetime checklist. In fact, most people who skydive, never go a second time. Most people enjoy it, but it does not re-enter the checklist. They say they’ll go, but unless they fall in love, or find a friend to go again, or put it back on the checklist for the next monumental life event, they won’t go again. But for those that are into it, they find a way to go again –and often.
For me, physical, mental and spiritual fitness is part of skydiving. What started with me taking care of my physical well being turned into me hiring a fitness coach. Why not get help? He set up a healthy routine and then surprised me by helping turn my mindset around. Why did I over-consume? I stopped moralizing food and stopped (or at least reduced) stress eating.
A solo skydiver has to be more physically fit than most people realize. We all think gravity simply drags us gracefully toward the earth and the parachute does all the work. That’s the way it works in movies, right? And while you cannot skydive without gravity and a parachute, the muscle and self control is paramount to making it graceful. The most likely position if you fall from an airplane? Spiraling on your back. The first responsibility of solo skydiving? Pull! Spiraling on your back is dangerous on multiple levels… foremost among them is forgetting to pull! When you go on a tandem skydive, the professional instructor is guiding you –the student– the whole way. When you go solo the first time, you have assistance in part but not the whole. And ultimately, it’s your butt on the line. Are you mentally, physically and spiritually ready to engage your whole being? Can you keep yourself under control when it’s all on the line?
I got myself mentally ready to go once. After we landed on the first jump I was immediately ready to go again. Yes. I can do this. My first tandem was at Skydive the Rock in Beloit, Wisconsin. I chose this location because it was small. If I chickened out the video proof could be contained. I was also extremely confident in our instructors… and in their demeanor related to my pent up anxiety surrounding my first jump. I wasn’t doing this on a whim. I’d been around the sport for years now. I knew about the injuries and risks. I had begun learning to pack. I knew about airplanes. I knew enough to know what I was getting into… and that there was very serious risk –even death. But, I still wanted to do it. I wanted someone in the airplane that wasn’t going to tease me or annoy the shit out of me prior to the jump… or dare I say, after the jump if I didn’t like it.
Now that I’ve been in the sport for a few years, I believe there are two major divisions of licensed skydivers. The athlete and the adrenaline junky. The athlete is more methodical and wants mastery of their body and the sport. While the adrenaline hits everyone, just as a pregame butterfly puts knots in your stomach, those that are in it for the adrenaline alone have a tendency to push too hard, too fast and get hurt. As manager Ted likes to say, “there’s no old and bold skydivers.” I’m firmly in the athlete mindset here. Get a little better. Live to do it again.
The moment I first landed safely I wanted to go again. I wanted to do it again. And I wanted to get better at it. Unfortunately, I was the last jump of the weekend at this location. Sadness. So, I went to Skydive Indianapolis the next weekend. We had a weird exit (my foot got tangled up in a seat belt) and the delay in the exit, and being the last out, meant we almost didn’t make it back to the dropzone. Thus, we had a very boring, straight line canopy flight back. But, we landed safely and my instructor did what he had to do to keep it as safe. I still liked it. “Well,” I thought, “I’ll just have to go again.” So, a few days later, I spent the weekend at Skydive Kansas City. I wore an altimeter and deployed the parachute. But, my legs were a mess. I needed more training. A lot more. That same day I jumped two more times with a tandem examiner. He taught me a ton. Legs. Spotting. Heading control. Landing patterns, etc. By this point, I was standing outside the aircraft, timing our exit, deploying, piloting the parachute to the holding area, etc. I was no longer on a roller coaster thrill ride. I was becoming a skydiver. On our sunset dive I deployed at the target 7,000 feet altitude and flew us nearly the whole way. That was my last tandem. I can land on my own. Let’s do this solo.
I came back to Indiana and signed up for one of our online first jump courses. Rocked it. I could study alone. Get my head around the finer details. Ordered the USPA SIM. Read it. I studied the science even more. I was getting into the weeds. The next week I was enrolled in our first jump course at Skydive Indianapolis. One of our instructors taught me and another student –a 60 year old civil engineer. This fellow had not even been on a tandem yet but he rocked the quizzes. Smart guy. But would he like it? I couldn’t believe he would just sign up for this. Wild. Cheers, dude. I jumped with two AFF Instructors soon thereafter. He stayed home to work on his physical ability. Good idea. I continued jumping. I continued improving. Jump again. Again. Do it again. Add skills. Learn. Execute. Jump again. Land. Jump again. At this point, I’m stretching and working out at home with the purpose to improve my skydives. I kept up on my USPA quizzes and began running through emergency procedures in my mind. I wound up completing AFF within 19 days –the fastest student from first solo to complete at any of our dropzones this year. They told me I needed 25 solo jumps instead of just 25 jumps. Rather than argue the book, I said, “who cares how many I need. I’m just going to keep jumping anyways.”
My father asked me, “when does skydiving begin to interfere with work?” I laughed. I’m pretty sure this is my job. When does me driving between our locations interfere with work? I like that, too. I’ve seen our tandem instructors exclaim under canopy how much they love their job. There’s literally no other thing in the world like it. Best comparisons? Having a baby. Getting married. Sex. It just blows your mind every time. What in the world did I just do? And how can we do that again?
The reality of owning and managing drop zones is that it’s a ton of work punctuated with sparks. We have amazing teammates that love this sport and love teaching other people how to engage their whole mind, body and spirit into living their lives to the fullest, while maintaining self control. I’m now in that camp –all the way. And while, I probably won’t accumulate tens of thousands of jumps, I’m not against it either. 😉